The more I think about it, Midori was kinda an idiot and not even because the players fooled him during the banquet. Midori likes to act powerful and like he's always the one in control, but then you remember his job description is 90% just:
Die
And when you really think about it, it doesn't seem like ASUNARO valued or liked him. I mean, if nothing else, they at least trusted him to go and get all the participants to sign a consent form, which, from what we know, was a pretty important task, but aside from that, ASUNARO really just told him
Like, at least the other floor masters, Miley and Gashu weren't just flat out told to die (Gashu just sorta decided to, anyways). It really makes you wonder how ASUNARO viewed Midori. From what we know, he was originally intended to be a participant himself until he "died", which just further implies that ASUNARO was itching to get rid of him. Who replaced him, if anyone (ASUNARO could have planned for 21 participants, counting Midori, or they replaced him with Kai), is unclear, but if Kai was meant to serve as a substitute for him as ASUNARO's traitor within the participants, and knowing how Kai was considered a non-candidate who wasn't meant to win (and we all know what happens to losers in the death game), it all just heavily supports the idea that ASUNARO wanted nothing more than to kill him off.
If you were working for a company that wanted nothing more than to put you in situations where you were all but guaranteed to die, you wouldn't want to work there anymore, would you? But Midori does. That plus his overwhelming fear of death, makes him look like a really big idiot, and to be honest, I think he may really be one. Sure, he's smart in a lot of ways, being skilled at manipulation and pressing people's buttons, not to mention reprogramming Maple forget her original purpose is to kill him, but he also just couldn't see that his boss clearly had it out for him.
So if they hate him so much, why even hire him? I believe, that in Kai's mini-episode, a silhouetted figure appears whose hair resembles Midori's. This has led many to believe she is Midori's mother (which might explain why he's so screwed up, if he was raised in ASUNARO). If his mom already worked there, and probably outranked Gashu, that could have influenced ASUNARO's decision when it came to employing Midori.
AKA Midori is a nepo-baby.
ASUNARO hired him even though they didn't want to and either his mom didn't actually care that much about him (otherwise she might have objected to the killing of her son) or has retired or died and then ASUNARO had an employee who they don't want nor need. In other words Midori's relationship with his employers is more like
As the only floor master whose death is actively sought out by ASUNARO, Midori might actually be pretty low down on the totem pole, I'd say below the other two floor masters, but just above Ranger and Safalin who aren't really floor masters. Midori clearly doesn't understand that ASUNARO would 100% let him die, seeing as how he pleaded to Meister right before he died. At the end of the day, to them he's just a problem child they can finally do away with. The experiments ASUNARO let him do on other people "until they broke or he got bored" were probably just ASUNARO keeping him entertained to shut him up for a while, more or less treating him like a literal kid.
The more I think about it, ASUNARO clearly values Midori especially little, and it's honestly a little funny to think about. Him and his experiments really just make him the death game equivalent of a tablet kid.
